Well first of all with the p2p servers and summoning the guys ping has to match with yours in the first place other wise it just won't show so if you have some friends from the US version of Demon's souls but are in the EU then you'll probably never summon them in DKS.
Also each time you load a game your randomly assigned to a server, if you and your friend are in different servers then you'll just not see them even after meeting all requirements. So I don't think redropping your sign will doing anything. What you'd have to do is one of you reloads the game instead, which still has a high chance of it never, working, summoning failed - the usual shi-...
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